The present invention relates to novel herbicidal compounds, to processes for their preparation, to herbicidal compositions which comprise the novel compounds, and to their use for controlling weeds, in particular in crops of useful plants, or for inhibiting plant growth.

Substituted thiazolopyridines are known from WO2021/204589. The present invention relates to novel isothiazolopyridine compounds. Thus, according to the present invention there is provided a compound of Formula (I): or an agronomically acceptable salt thereof, wherein

R ¹ is selected from the group consisting of Cs-Cs cycloalkenyl, phenyl and a five or six-membered heteroaryl, the heteroaryl containing from one to three heteroatoms each independently selected from the group consisting of oxygen, nitrogen and sulphur, and wherein the Cs-Cs cycloalkenyl, phenyl and heteroaryl may be optionally substituted by one or more R ³ substituents;

R ² is selected from the group consisting of hydrogen, halogen, cyano, Ci- Cealkyl-, Ci-Cehaloalkyl-, C2-Cealkenyl-, C2-Cehaloalkenyl-, C2-Cealkynyl-, C2- Cehaloalkynyl-, Ci-Cealkoxy-, Ci-Cehaloalkoxy- and Cs-Cecycloalkyl;

R ³ is selected from the group consisting of halogen, Ci-Cealkyl-, C2-Cealkenyl- , C2-Cealkynyl-, Ci-Cehaloalkyl-, C2-Cehaloalkenyl-, Ci-Cealkoxy-, C1- Cehaloalkoxy-, Ci-CealkoxyCi-Csalkoxy-, Ci-CealkoxyCi-Csalkyl-, C1- Cehaloalkoxy-, Ci-C6alkyl-S(O) _p -, Cs-Cecycloalkyl-, cyano and nitro; and p is 0, 1 or 2.

Ci-Cealkyl- includes, for example, methyl (Me, CH3), ethyl (Et, C2H5), n-propyl (n-Pr), isopropyl (/-Pr), n-butyl (n-Bu), isobutyl (/-Bu), sec-butyl and terf-butyl (t-Bu). Ci-C2alkyl is methyl (Me, CH3) or ethyl (Et, C2H5).

C2-Cealkenyl- includes, for example, -CH=CH2 (vinyl) and -CH2-CH=CH2 (allyl).

C2-Cealkynyl- refers to a straight or branched hydrocarbon chain radical group consisting solely of carbon and hydrogen atoms, containing at least one triple bond, having from two to four carbon atoms, and which is attached to the rest of the molecule by a single bond. Examples of C2-C4alkynyl include, but are not limited to, prop-1 -ynyl, propargyl (prop-2-ynyl), and but-1-ynyl.

Halogen (or halo) includes, for example, fluorine, chlorine, bromine or iodine. The same correspondingly applies to halogen in the context of other definitions, such as haloalkyl.

Ci-Cehaloalkyl- includes, for example, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2,2,2-trifluoroethyl, 2- fluoroethyl, 2-chloroethyl, pentafluoroethyl, 1 , 1 -difluoro-2,2,2-trichloroethyl, 2, 2,3,3- tetrafluoropropyl and 2,2,2-trichloroethyl and heptafluoro-n-propyl. Ci-C2haloalkyl is, for example, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2,2,2-trifluoroethyl, 2-fluoroethyl, 2-chloroethyl, pentafluoroethyl, or 1 , 1 -difluoro-2,2,2-trichloroethyl.

Ci-Cealkoxy includes methoxy and ethoxy.

Ci-Cehaloalkoxy- includes, for example, fluoromethoxy, difluoromethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy, 1 ,1 ,2,2-tetrafluoroethoxy, 2-fluoroethoxy, 2- chloroethoxy, 2,2-difluoroethoxy or 2,2,2-trichloroethoxy, preferably difluoromethoxy, 2-chloroethoxy or trifluoromethoxy.

Cs-Cecycloalkyl includes cyclopropyl, cyclopentyl and cyclohexyl.

Cs-Cs cycloalkenyl includes cyclopentenyl and cyclohexenyl. Ci-C4alkyl-S- (alkylthio) includes, for example, methylthio, ethylthio, propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio or tert-butylthio, preferably methylthio or ethylthio.

Ci-C4alkyl-S(O)- (alkylsulfinyl) includes, for example, methylsulfinyl, ethylsulfinyl, propylsulfinyl, isopropylsulfinyl, n-butylsulfinyl, isobutylsulfinyl, secbutylsulfinyl or tert-butylsulfinyl, preferably methylsulfinyl or ethylsulfinyl.

Ci-C4alkyl-S(O)2- (alkylsulfonyl) includes, for example, methylsulfonyl, ethylsulfonyl, propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, isobutylsulfonyl, secbutylsulfonyl or tert-butylsulfonyl, preferably methylsulfonyl or ethylsulfonyl.

In one embodiment of the present invention, there is provided a compound of Formula (I), wherein R ¹ is a five or six-membered heteroaryl selected from the group consisting of furanyl, pyrrolyl, tetrazolyl, thiophenyl, thiazolyl, thiadiazolyl, oxazolyl, isoxazolyl, thiazolyl, pyrazolyl, isothiazolyl, pyridyl, pyridazinyl, pyrazinyl, pyrimidinyl and triazolyl each of which is optionally substituted by one or more (e.g 1, 2 or 3) independent R ³ substituents. In a preferred embodiment, R ¹ is thiophenyl optionally substituted by one or more (e.g 1, 2 or 3) independent R ³ substituents.

In a preferred embodiment of the present invention, there is provided a compound of Formula (I), wherein R ¹ is phenyl which is optionally substituted by one or more (e.g 1 , 2 or 3) independent R ³ substituents. In a more preferred embodiment of the present invention, R ¹ is phenyl which is substituted by one or more (e.g 1 , 2 or 3) independent R ³ substituents. In a still more preferred embodiment, R ¹ is phenyl which is substituted by one R ³ substituent in the 2-position of the phenyl ring, preferably a 2-halo substituent and most preferably 2-fluoro.

In another preferred embodiment of the present invention, there is provided a compound of Formula (I), wherein R ² is halogen or Ci-Cealkyl-. In a more preferred embodiment, R ² is halogen (e.g F, Cl, Br) or Ci-C2alkyl- (methyl or ethyl).

In another preferred embodiment of the present invention, R ³ is halogen (e.g fluoro). In a particularly preferred embodiment of the present invention, there is provided a compound of Formula (I) wherein R ¹ is phenyl optionally substituted by one or more R ³ and R ² is halogen or Ci-C2alkyl-. In a still more preferred embodiment, there is provided a compound of Formula (I) wherein R ¹ is 2-substituted -phenyl- (preferably 2-F-phenyl) and R ² is halogen or Ci-C2alkyl-, preferably methyl.

Compounds of Formula (I) may contain asymmetric centres and may be present as a single enantiomer, pairs of enantiomers in any proportion or, where more than one asymmetric centre are present, contain diastereoisomers in all possible ratios. Typically, one of the enantiomers has enhanced biological activity compared to the other possibilities.

The present invention also provides agronomically acceptable salts of compounds of Formula (I). Salts that the compounds of Formula (I) may form with amines, including primary, secondary and tertiary amines (for example ammonia, dimethylamine and triethylamine), alkali metal and alkaline earth metal bases, transition metals or quaternary ammonium bases are preferred.

The compounds of Formula (I) according to the invention can be used as herbicides by themselves, but they are generally formulated into herbicidal compositions using formulation adjuvants, such as carriers, solvents and surfaceactive agents (SAA). Thus, the present invention further provides a herbicidal composition comprising a herbicidal compound according to any one of the previous claims and an agriculturally acceptable formulation adjuvant. The composition can be in the form of concentrates which are diluted prior to use, although ready-to-use compositions can also be made. The final dilution is usually made with water, but can be made instead of, or in addition to, water, with, for example, liquid fertilisers, micronutrients, biological organisms, oil or solvents.

The herbicidal compositions generally comprise from 0.1 to 99 % by weight, especially from 0.1 to 95 % by weight, compounds of Formula I and from 1 to 99.9 % by weight of a formulation adjuvant which preferably includes from 0 to 25 % by weight of a surface-active substance.

The compositions can be chosen from a number of formulation types. These include an emulsion concentrate (EC), a suspension concentrate (SC), a suspo- emulsion (SE), a capsule suspension (CS), a water dispersible granule (WG), an emulsifiable granule (EG), an emulsion, water in oil (EO), an emulsion, oil in water (EW), a micro-emulsion (ME), an oil dispersion (OD), an oil miscible flowable (OF), an oil miscible liquid (OL), a soluble concentrate (SL), an ultra-low volume suspension (Sil), an ultra-low volume liquid (UL), a technical concentrate (TK), a dispersible concentrate (DC), a soluble powder (SP), a wettable powder (WP) and a soluble granule (SG). The formulation type chosen in any instance will depend upon the particular purpose envisaged and the physical, chemical and biological properties of the compound of Formula (I).

Soluble powders (SP) may be prepared by mixing a compound of Formula (I) with one or more water-soluble inorganic salts (such as sodium bicarbonate, sodium carbonate or magnesium sulphate) or one or more water-soluble organic solids (such as a polysaccharide) and, optionally, one or more wetting agents, one or more dispersing agents or a mixture of said agents to improve water dispersibility/solubility. The mixture is then ground to a fine powder. Similar compositions may also be granulated to form water soluble granules (SG).

Wettable powders (WP) may be prepared by mixing a compound of Formula (I) with one or more solid diluents or carriers, one or more wetting agents and, preferably, one or more dispersing agents and, optionally, one or more suspending agents to facilitate the dispersion in liquids. The mixture is then ground to a fine powder. Similar compositions may also be granulated to form water dispersible granules (WG).

Granules (GR) may be formed either by granulating a mixture of a compound of Formula (I) and one or more powdered solid diluents or carriers, or from preformed blank granules by absorbing a compound of Formula (I) (or a solution thereof, in a suitable agent) in a porous granular material (such as pumice, attapulgite clays, fuller's earth, kieselguhr, diatomaceous earths or ground corn cobs) or by adsorbing a compound of Formula (I) (or a solution thereof, in a suitable agent) on to a hard core material (such as sands, silicates, mineral carbonates, sulphates or phosphates) and drying if necessary. Agents which are commonly used to aid absorption or adsorption include solvents (such as aliphatic and aromatic petroleum solvents, alcohols, ethers, ketones and esters) and sticking agents (such as polyvinyl acetates, polyvinyl alcohols, dextrins, sugars and vegetable oils). One or more other additives may also be included in granules (for example an emulsifying agent, wetting agent or dispersing agent). Dispersible Concentrates (DC) may be prepared by dissolving a compound of Formula (I) in water or an organic solvent, such as a ketone, alcohol or glycol ether. These solutions may contain a surface-active agent (for example to improve water dilution or prevent crystallisation in a spray tank).

Emulsifiable concentrates (EC) or oil-in-water emulsions (EW) may be prepared by dissolving a compound of Formula (I) in an organic solvent (optionally containing one or more wetting agents, one or more emulsifying agents or a mixture of said agents). Suitable organic solvents for use in ECs include aromatic hydrocarbons (such as alkylbenzenes or alkylnaphthalenes, exemplified by SOLVESSO 100, SOLVESSO 150 and SOLVESSO 200; SOLVESSO is a Registered Trade Mark), ketones (such as cyclohexanone or methylcyclohexanone) and alcohols (such as benzyl alcohol, furfuryl alcohol or butanol), N-alkylpyrrolidones (such as N-methylpyrrolidone or N-octylpyrrolidone), dimethyl amides of fatty acids (such as Cs-Cio fatty acid dimethylamide) and chlorinated hydrocarbons. An EC product may spontaneously emulsify on addition to water, to produce an emulsion with sufficient stability to allow spray application through appropriate equipment.

Preparation of an EW involves obtaining a compound of Formula (I) either as a liquid (if it is not a liquid at room temperature, it may be melted at a reasonable temperature, typically below 70°C) or in solution (by dissolving it in an appropriate solvent) and then emulsifying the resultant liquid or solution into water containing one or more SAAs, under high shear, to produce an emulsion. Suitable solvents for use in EWs include vegetable oils, chlorinated hydrocarbons (such as chlorobenzenes), aromatic solvents (such as alkylbenzenes or alkylnaphthalenes) and other appropriate organic solvents which have a low solubility in water.

Microemulsions (ME) may be prepared by mixing water with a blend of one or more solvents with one or more SAAs, to produce spontaneously a thermodynamically stable isotropic liquid formulation. A compound of Formula (I) is present initially in either the water or the solvent/SAA blend. Suitable solvents for use in MEs include those hereinbefore described for use in in ECs or in EWs. An ME may be either an oil-in-water or a water-in-oil system (which system is present may be determined by conductivity measurements) and may be suitable for mixing water- soluble and oil-soluble pesticides in the same formulation. An ME is suitable for dilution into water, either remaining as a microemulsion or forming a conventional oil- in-water emulsion. Suspension concentrates (SC) may comprise aqueous or non-aqueous suspensions of finely divided insoluble solid particles of a compound of Formula (I). SCs may be prepared by ball or bead milling the solid compound of Formula (I) in a suitable medium, optionally with one or more dispersing agents, to produce a fine particle suspension of the compound. One or more wetting agents may be included in the composition and a suspending agent may be included to reduce the rate at which the particles settle. Alternatively, a compound of Formula (I) may be dry milled and added to water, containing agents hereinbefore described, to produce the desired end product.

Aerosol formulations comprise a compound of Formula (I) and a suitable propellant (for example n-butane). A compound of Formula (I) may also be dissolved or dispersed in a suitable medium (for example water or a water miscible liquid, such as n-propanol) to provide compositions for use in non-pressurised, hand-actuated spray pumps.

Capsule suspensions (CS) may be prepared in a manner similar to the preparation of EW formulations but with an additional polymerisation stage such that an aqueous dispersion of oil droplets is obtained, in which each oil droplet is encapsulated by a polymeric shell and contains a compound of Formula (I) and, optionally, a carrier or diluent therefor. The polymeric shell may be produced by either an interfacial polycondensation reaction or by a coacervation procedure. The compositions may provide for controlled release of the compound of Formula (I) and they may be used for seed treatment. A compound of Formula (I) may also be formulated in a biodegradable polymeric matrix to provide a slow, controlled release of the compound.

The composition may include one or more additives to improve the biological performance of the composition, for example by improving wetting, retention or distribution on surfaces; resistance to rain on treated surfaces; or uptake or mobility of a compound of Formula (I). Such additives include surface active agents (SAAs), spray additives based on oils, for example certain mineral oils or natural plant oils (such as soy bean and rape seed oil), modified plant oils such as methylated rape seed oil (MRSO), and blends of these with other bio-enhancing adjuvants (ingredients which may aid or modify the action of a compound of Formula (I).

Wetting agents, dispersing agents and emulsifying agents may be SAAs of the cationic, anionic, amphoteric or non-ionic type. Suitable SAAs of the cationic type include quaternary ammonium compounds (for example cetyltrimethyl ammonium bromide), imidazolines and amine salts.

Suitable anionic SAAs include alkali metals salts of fatty acids, salts of aliphatic monoesters of sulphuric acid (for example sodium lauryl sulphate), salts of sulphonated aromatic compounds (for example sodium dodecylbenzenesulphonate, calcium dodecylbenzenesulphonate, butylnaphthalene sulphonate and mixtures of sodium di-/sopropyl- and tri-/sopropyl-naphthalene sulphonates), ether sulphates, alcohol ether sulphates (for example sodium laureth-3-sulphate), ether carboxylates (for example sodium laureth-3-carboxylate), phosphate esters (products from the reaction between one or more fatty alcohols and phosphoric acid (predominately mono-esters) or phosphorus pentoxide (predominately di-esters), for example the reaction between lauryl alcohol and tetraphosphoric acid; additionally these products may be ethoxylated), sulphosuccinamates, paraffin or olefine sulphonates, taurates, lignosulphonates and phosphates I sulphates of tristyrylphenols.

Suitable SAAs of the amphoteric type include betaines, propionates and glycinates.

Suitable SAAs of the non-ionic type include condensation products of alkylene oxides, such as ethylene oxide, propylene oxide, butylene oxide or mixtures thereof, with fatty alcohols (such as oleyl alcohol or cetyl alcohol) or with alkylphenols (such as octylphenol, nonylphenol or octylcresol); partial esters derived from long chain fatty acids or hexitol anhydrides; condensation products of said partial esters with ethylene oxide; block polymers (comprising ethylene oxide and propylene oxide); alkanolamides; simple esters (for example fatty acid polyethylene glycol esters); amine oxides (for example lauryl dimethyl amine oxide); lecithins and sorbitans and esters thereof, alkyl polyglycosides and tristyrylphenols.

Suitable suspending agents include hydrophilic colloids (such as polysaccharides, polyvinylpyrrolidone or sodium carboxymethylcellulose) and swelling clays (such as bentonite or attapulgite).

The compounds of present invention can also be used in mixture with one or more additional herbicides and/or plant growth regulators. Examples of such additional herbicides or plant growth regulators include acetochlor, acifluorfen (including acifluorfen-sodium), aclonifen, ametryn, amicarbazone, aminopyralid, aminotriazole, atrazine, beflubutamid-M, benquitrione, bensulfuron (including bensulfuron-methyl), bentazone, bicyclopyrone, bilanafos, bipyrazone, bispyribac-sodium, bixlozone, bromacil, bromoxynil, butachlor, butafenacil, carfentrazone (including carfentrazone- ethyl), cloransulam (including cloransulam-methyl), chlorimuron (including chlorimuron-ethyl), chlorotoluron, chlorsulfuron, cinmethylin, clacyfos, clethodim, clodinafop (including clodinafop-propargyl), clomazone, clopyralid, cyclopyranil, cyclopyrimorate, cyclosulfamuron, cyhalofop (including cyhalofop-butyl), 2,4-D (including the choline salt and 2-ethylhexyl ester thereof), 2,4-DB, desmedipham, dicamba (including the aluminium, aminopropyl, bis-aminopropylmethyl, choline, dichloroprop, diglycolamine, dimethylamine, dimethylammonium, potassium and sodium salts thereof) diclosulam, diflufenican, diflufenzopyr, dimethachlor, dimethenamid-P, dioxopyritrione, diquat dibromide, diuron, epyrifenacil, ethalfluralin, ethofumesate, fenoxaprop (including fenoxaprop-P-ethyl), fenoxasulfone, fenpyrazone, fenquinotrione, fentrazamide, flazasulfuron, florasulam, florpyrauxifen (including florpyrauxifen-benzyl), fluazifop (including fluazifop-P-butyl), flucarbazone (including flucarbazone-sodium), flufenacet, flumetsulam, flumioxazin, fluometuron, fomesafen, flupyrsulfuron (including flupyrsulfuron-methyl-sodium), fluroxypyr (including fluroxypyr-meptyl), fomesafen, foramsulfuron, glufosinate (including L-glufosinate and the ammonium salts of both), glyphosate (including the diammonium, isopropylammonium and potassium salts thereof), halauxifen (including halauxifen-methyl), haloxyfop (including haloxyfop-methyl), hexazinone, hydantocidin, imazamox (including R-imazamox), imazapic, imazapyr, imazethapyr, indaziflam, iodosulfuron (including iodosulfuron-methyl-sodium), iofensulfuron (including iofensulfuron-sodium), ioxynil, isoproturon, isoxaflutole, lancotrione, MCPA, MCPB, mecoprop-P, mesosulfuron (including mesosulfuron-methyl), mesotrione, metamitron, metazachlor, methiozolin, metolachlor, metosulam, metribuzin, metsulfuron, napropamide, nicosulfuron, norflurazon, oxadiazon, oxasulfuron, oxyfluorfen, paraquat dichloride, pendimethalin, penoxsulam, phenmedipham, picloram, pinoxaden, pretilachlor, primisulfuron-methyl, prometryne, propanil, propaquizafop, propyrisulfuron, propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen (including pyraflufen-ethyl), pyrasulfotole, pyridate, pyriftalid, pyrimisulfan, pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quizalofop (including quizalofop-P-ethyl and quizalofop-P-tefuryl), rimisoxafen, rimsulfuron, saflufenacil, sethoxydim, simazine, S-metalochlor, sulfentrazone, sulfosulfuron, tebuthiuron, tefuryltrione, tembotrione, terbuthylazine, terbutryn, tetflupyrolimet, thiencarbazone, thifensulfuron, tiafenacil, tolpyralate, topramezone, tralkoxydim, triafamone, triallate, triasulfuron, tribenuron (including tribenuron-methyl), triclopyr, trifloxysulfuron (including trifloxysulfuron-sodium), trifludimoxazin, trifluralin, triflusulfuron, tripyrasulfone, 3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4- trifluoromethyl-3,6-dihydropyrimidin-1(2H)-yl)phenyl)-5-meth yl-4,5-dihydroisoxazole- 5-carboxylic acid ethyl ester, 4-hydroxy-1-methoxy-5-methyl-3-[4-(trifluoromethyl)-2- pyridyl]imidazolidin-2-one, 4-hydroxy-1,5-dimethyl-3-[4-(trifluoromethyl)-2-pyridyl]- imidazolidine-2-one, 5-ethoxy-4-hydroxy-1-methyl-3-[4-(trifluoromethyl)-2-pyridyl ]- imidazolidin-2-one, 4-hydroxy-1-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazol idin-2- one, 4-hydroxy-1,5-dimethyl-3-[1-methyl-5-(trifluoromethyl)pyrazo l-3-yl]imidazolidin-

2-one, (4R)1-(5-tert-butylisoxazol-3-yl)-4-ethoxy-5-hydroxy-3-methy l-imidazolidin-2- one, 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1 H-indol-6-yl)pyridine-2-carboxylic acid (including agrochemically acceptable esters thereof, for example, methyl 4-amino-3- chloro-5-fluoro-6-(7-fluoro-1 H-indol-6-yl)pyridine-2-carboxylate, prop-2-ynyl 4-amino-

3-chloro-5-fluoro-6-(7-fluoro-1 H-indol-6-yl)pyridine-2-carboxylate and cyanomethyl 4- amino-3-chloro-5-fluoro-6-(7-fluoro-1 H-indol-6-yl)pyridine-2-carboxylate), 3-ethyl- sulfanyl-N-(1 ,3,4-oxadiazol-2-yl)-5-(trifluoromethyl)-[1,2,4]triazolo[4,3 -a]pyridine-8- carboxamide, 3-(isopropylsulfanylmethyl)-N-(5-methyl-1 ,3,4-oxadiazol-2-yl)-5- (trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine-8-carboxami de, 3-(isopropylsulfonyl- methyl)-N-(5-methyl-1,3,4-oxadiazol-2-yl)-5-(trifluoromethyl )-[1,2,4]triazolo[4,3-a]- pyridine-8-carboxamide, 3-(ethylsulfonylmethyl)-N-(5-methyl-1 ,3,4-oxadiazol-2-yl)-5- (trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine-8-carboxami de, ethyl-2-[[3-[[3-chloro-5- fluoro-6-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1- yl]-2-pyridyl]oxy]acetate,6- chloro-4-(2,7-dimethyl-1-naphthyl)-5-hydroxy-2-methyl-pyrida zin-3-one, tetrahydro- furan-2-ylmethyl(2R)-2-[(4-amino-3,5-dichloro-6-fluoro-2-pyr idyl)oxy]-propanoate, (2R)-2-[(4-amino-3,5-dichloro-6-fluoro-2-pyridyl)oxy]propano ic acid, tetrahydrofuran- 2-ylmethyl2-[(4-amino-3,5-dichloro-6-fluoro-2-pyridyl)oxy]pr opanoate, 2-[(4-amino- 3,5-dichloro-6-fluoro-2-pyridyl)oxy]propanoic acid, 2-fluoro-N-(5-methyl-1 ,3,4- oxadiazol-2-yl)-3-[(R)-propylsulfinyl]-4-(trifluoromethyl)be nzamide, 2-fluoro-N-(5- methyl-1,3,4-oxadiazol-2-yl)-3-propylsulfinyl-4-(trifluorome thyl)benzamide, (2- fluorophenyl)methyl6-amino-5-chloro-2-(4-chloro-2-fluoro-3-m ethoxyphenyl)- pyrimidine-4-carboxylate, 6-amino-5-chloro-2-(4-chloro-2-fluoro-3-methoxy-phenyl)- pyrimidine-4-carboxylic acid, 3-(3-chlorophenyl)-6-(5-hydroxy-1 ,3-dimethyl-pyrazole-

4-carbonyl)-1 ,5-dimethyl-quinazoline-2, 4-dione and [4-[3-(3-chlorophenyl)-1 ,5- dimethyl-2,4-dioxo-quinazoline-6-carbonyl]-2,5-dimethyl-pyra zol-3-yl]N,N- diethylcarbamate.

The mixing partners of the compound of Formula (I) may also be in the form of esters or salts, as mentioned e.g. in The Pesticide Manual, Sixteenth Edition, British Crop Protection Council, 2012. The compound of Formula (I) can also be used in mixtures with other agrochemicals such as fungicides, nematicides or insecticides, examples of which are given in The Pesticide Manual.

The mixing ratio of the compound of Formula (I) to the mixing partner is preferably from 1: 100 to 1000:1.

The mixtures can advantageously be used in the above-mentioned formulations (in which case "active ingredient" relates to the respective mixture of compound of Formula (I) with the mixing partner).

The compounds or mixtures of the present invention can also be used in combination with one or more herbicide safeners. Examples of such safeners include benoxacor, cloquintocet (including cloquintocet-mexyl), cyprosulfamide, dichlormid, fenchlorazole (including fenchlorazole-ethyl), fenclorim, fluxofenim, furilazole, isoxadifen (including isoxadifen-ethyl), mefenpyr (including mefenpyr-diethyl), metcamifen and oxabetrinil.

Particularly preferred are mixtures of a compound of Formula (I) with cyprosulfamide, isoxadifen-ethyl, cloquintocet-mexyl and/or metcamifen.

The safeners of the compound of Formula (I) may also be in the form of esters or salts, as mentioned e.g. in The Pesticide Manual, 16 ^th Edition (BCPC), 2012. The reference to cloquintocet-mexyl also applies to a lithium, sodium, potassium, calcium, magnesium, aluminium, iron, ammonium, quaternary ammonium, sulfonium or phosphonium salt thereof as disclosed in WO 02/34048.

Preferably the mixing ratio of compound of Formula (I) to safener is from 100: 1 to 1 : 10, especially from 20: 1 to 1 :1.

The present invention still further provides a method of controlling weeds at a locus said method comprising applying to the locus a weed controlling amount of a composition comprising a compound of Formula (I). Moreover, the present invention may further provide a method of selectively controlling weeds at a locus comprising crop plants and weeds, wherein the method comprises application to the locus of a weed controlling amount of a composition according to the present invention. ‘Controlling’ means killing, reducing or retarding growth or preventing or reducing germination. It is noted that the compounds of the present invention show a much- improved selectivity compared to know, structurally similar compounds. Generally the plants to be controlled are unwanted plants (weeds). ‘Locus’ means the area in which the plants are growing or will grow. The application may be applied to the locus preemergence and/or postemergence of the crop plant. Some crop plants may be inherently tolerant to herbicidal effects of compounds of Formula (I). Preferred crop plants include maize, wheat, barley soybean and rice.

The rates of application of compounds of Formula I may vary within wide limits and depend on the nature of the soil, the method of application (pre- or postemergence; seed dressing; application to the seed furrow; no tillage application etc.), the crop plant, the weed(s) to be controlled, the prevailing climatic conditions, and other factors governed by the method of application, the time of application and the target crop. The compounds of Formula I according to the invention are generally applied at a rate of from 10 to 2500 g/ha, especially from 25 to 1000 g/ha, more especially from 25 to 250 g/ha.

The application is generally made by spraying the composition, typically by tractor mounted sprayer for large areas, but other methods such as dusting (for powders), drip or drench can also be used.

Crop plants are to be understood as also including those crop plants which have been rendered tolerant to other herbicides or classes of herbicides (e.g. ALS-, GS-, EPSPS-, PPO-, HPPD-, -PDS , -SDPS and ACCase-inhibitors) by conventional methods of breeding or by genetic engineering. An example of a crop that has been rendered tolerant to imidazolinones, e.g. imazamox, by conventional methods of breeding is Clearfield® summer rape (canola). Examples of crops that have been rendered tolerant to herbicides by genetic engineering methods include e.g. glyphosate- and glufosinate-resistant maize varieties commercially available under the trade names RoundupReady® and LibertyLink®.

Crop plants are also to be understood as being those which have been rendered resistant to harmful insects by genetic engineering methods, for example Bt maize (resistant to European corn borer), Bt cotton (resistant to cotton boll weevil) and also Bt potatoes (resistant to Colorado beetle). Examples of Bt maize are the Bt 176 maize hybrids of NK® (Syngenta Seeds). The Bt toxin is a protein that is formed naturally by Bacillus thuringiensis soil bacteria. Examples of toxins, or transgenic plants able to synthesise such toxins, are described in EP-A-451 878, EP-A-374 753, WO 93/07278, WO 95/34656, WO 03/052073 and EP-A-427 529. Examples of transgenic plants comprising one or more genes that code for an insecticidal resistance and express one or more toxins are KnockOut® (maize), Yield Gard® (maize), NuCOTIN33B® (cotton), Bollgard® (cotton), NewLeaf® (potatoes), NatureGard® and Protexcta®. Plant crops or seed material thereof can be both resistant to herbicides and, at the same time, resistant to insect feeding (“stacked” transgenic events). For example, seed can have the ability to express an insecticidal Cry3 protein while at the same time being tolerant to glyphosate.

Crop plants are also to be understood to include those which are obtained by conventional methods of breeding or genetic engineering and contain so-called output traits (e.g. improved storage stability, higher nutritional value and improved flavour).

The compositions can be used to control unwanted plants (collectively, ‘weeds’). The weeds to be controlled may be both monocotyledonous species, for example Agrostis, Alopecurus, Avena, Brachiaria, Bromus, Cenchrus, Cyperus, Digitaria, Echinochloa, Eleusine, Lolium, Monochoria, Rottboellia, Sagittaria, Scirpus, Setaria and Sorghum, and dicotyledonous species, for example Abutilon, Amaranthus, Ambrosia, Chenopodium, Chrysanthemum, Conyza, Galium, Ipomoea, Nasturtium, Sida, Sinapis, Solanum, Stellaria, Veronica, Viola and Xanthium.

In a further aspect of the present invention there is provided the use of a compound of Formula (I) as defined herein as a herbicide.

Processes for preparation of compounds of Formula (I)

Processes for preparation of compounds, e.g. a compound of formula (I) (which optionally can be an agrochemically acceptable salt thereof), are now described, and form further aspects of the present invention.

Formula A Formula I

A compound of Formula I may be prepared from a compound of Formula A via a diazotisation reaction (and subsequent decomposition) using a suitable reagent and in a suitable solvent. Suitable reagents may include isopentyl nitrite or similar. Suitable solvents may include 1,4-dioxane or DMF.

Formula B Formula A

A compound of Formula A may be prepared from a compound of Formula B via a cyclisation reaction in the presence of a suitable oxidising agent and in a suitable solvent. Suitable oxidising agents may include aqueous hydrogen peroxide solution. Suitable solvents may include MeOH.

Formula C Formula B

A compound of Formula B may be prepared from a compound of Formula C by reaction with a suitable thionation reagent in a suitable solvent. Suitable thionation reagents may include ammonium sulfide. Suitable solvents may include pyridine.

Formula D Formula C

A compound of Formula C may be prepared from a compound of Formula D (where X ¹ represents a suitable halogen, such as Cl, Br or I) via a cyanation reaction using a suitable cyanide source and a suitable catalyst and a suitable base and in a suitable solvent. Suitable cyanide sources may include potassium ferricyanide. Suitable catalysts may include XPhos Pd G3. Suitable bases may include potassium acetate. Suitable solvents may include cyclopentylmethyl ether.

Formula E Formula D

A compound of Formula D (where X ¹ represents a suitable halogen, such as Cl, Br or I) may be prepared from a compound of Formula E by reaction with a suitable halogenation reagent in a suitable solvent. Suitable halogenation reagents may include Br2 (when X ¹ = Br). Suitable solvents may include acetic acid.

Formula F Formula E

A compound of Formula E may be prepared from a compound of Formula F (where X ² represents a suitable halogen or pseudohalogen, such as Cl, Br, I or OTf) via a cross-coupling reaction with a compound of Formula G (where Y ¹ represents a suitable cross-coupling group such as -B(OH)2) in the presence of a suitable catalyst and a suitable base and in a suitable solvent. Suitable catalysts may include tetrakis(triphenylphosphine)palladium(0). Suitable bases may include aqueous sodium carbonate. Suitable solvents may include 1,4-dioxane. Compounds of Formula F and of Formula G are commercially available or may be prepared by methods known in the literature.

Formuta H Formula C In an alternative approach, a compound of Formula C may be prepared from a compound of Formula H (where X ³ represents a suitable halogen or pseudohalogen, such as Cl, Br, I or OTf) via a cross-coupling reaction with a suitable ammonia equivalent in the presence of a suitable catalyst and ligand and a suitable base and in a suitable solvent. Suitable ammonia equivalents may include tert-butyl carbamate. Suitable catalysts may include Pd(OAc)2. Suitable ligands may include XPhos. Suitable bases may include CS2CO3. Suitable solvents may include toluene.

Formula J Formula H

A compound of Formula H may be prepared from a compound of Formula J (where X ² represents a suitable halogen or pseudohalogen, such as Cl, Br, I or OTf) via a cross-coupling reaction with a compound of Formula G (where Y ¹ represents a suitable cross-coupling group such as -B(OH)2) in the presence of a suitable catalyst and a suitable base and in a suitable solvent. Suitable catalysts may include tetrakis(triphenylphosphine)palladium(0). Suitable bases may include aqueous sodium or potassium carbonate. Suitable solvents may include 1 ,4-dioxane or toluene. Compounds of Formula J and of Formula G are commercially available or may be prepared by methods known in the literature.

The following non-limiting examples provide specific synthesis methods for representative compounds of the present invention, as referred to in Table 1 below.

Example 1 : Synthesis of 6-(2-fluorophenyl)-5-methyl-isothiazolo[3,4-b]pyridine (Compound 1.001)

Step 1 : Synthesis of 6-(2-fluorophenyl)-5-methyl-pyridin-2-amine

To stirred solution of 6-chloro-5-methyl-pyridin-2-amine (5.00 g, 35.07 mmol) and (2- fluorophenyl)boronic acid (5.40g, 38.57 mmol) in 1,4-dioxane (35 mL) was added a solution of 2M aqueous sodium carbonate (37.5 mL, 75 mmol). The reaction was then degassed with N2 and then tetrakis(triphenylphosphine)palladium(0) (2.09g, 1.75 mmol) was added. The reaction was heated at 100°C for 28 hours then allowed to cool to RT. The reaction was diluted with EtOAc, filtered through celite and washed with further EtOAc. The filtrate and washings were combined and washed with water. The aqueous layer was extracted with ethyl acetate, the combined organic extracts were concentrated under reduced pressure. The crude product was purified by flash chromatography on silica gel using a gradient of EtOAc/cyclohexane to give the desired product (2.0g, 25.3%).

¹ H NMR (400 MHz, CDCh) 6 7.43-7.31 (m, 3H), 7.21 (t, 1 H), 7.12 (t, 1 H), 6.46 (d, 1 H), 4.47 (br s, 2 H), 2.07 (s, 3H)

Step 2: Synthesis of 3-bromo-6-(2-fluorophenyl)-5-methyl-pyridin-2-amine

To a stirred solution of 6-(2-fluorophenyl)-5-methyl-pyridin-2-amine (3.5 g, 17.0 mmol) in acetic acid (12 mL) at RT was added Br2 (0.90 mL, 18 mmol). The reaction was stirred at RT for 3h then diluted with ice cold water and basified to pH 11 using 50 % aqueous sodium hydroxide solution. The reaction was then extracted with EtOAc (x3) and the combined organic extracts were washed with saturated sodium thiosulfate solution, dried over Na2SO4 and evaporated to dryness under reduced pressure. The crude product was then purified by flash chromatography on silica gel using a gradient of EtOAc/cyclohexane as eluent to give the desired product (2.30g, 43%). ¹ H NMR (400 MHz, CDCh) 6 7.60 (s, 1 H), 7.46-7.33 (m, 2H), 7.26-7.19 (m, 1 H), 7.13 (t, 1 H), 4.83 (br s, 2H), 2.09 (d, 3H).

Step 3: Synthesis of 2-amino-6-(2-fluorophenyl)-5-methyl-pyridine-3- carbonitrile

A microwave vial was charged with 3-bromo-6-(2-fluorophenyl)-5-methyl-pyridin-2- amine (1.0 g, 3.5 mmol), cyclopentyl methyl ether (10 mL) and water (10 mL). The reaction was degassed for 15 min with N2 and then potassium ferrocyanide (0.81 g, 2.1 mmol), XPhos Pd G3 (0.30 g, 0.35 mmol) and potassium acetate (0.044 g, 0.44 mmol) was added and the reaction heated to 120°C for 2 hr under microwave irradiation. The reaction was cooled to RT and partitioned between EtOAc (80 mL) and water (30 mL). The aqueous phase was further extracted with EtOAc (60 mL). The combined organic extracts were dried over Na2SO4 and evaporated to dryness under reduced pressure. The crude product was purified by flash chromatography on silica gel using a gradient of EtOAc/cyclohexane as eluent to give the desired product (235mg, 28%).

¹ H NMR (400 MHz, CDCh) 6 7.64 (s, 1H), 7.49-7.41 (m, 1 H), 7.38 (td, 1H), 7.30-7.25 (m, 1 H), 7.17 (ddd, 1 H), 5.13 (br s, 2H), 2.13 (d, 3H)

Step 4: Synthesis of 2-amino-6-(2-fluorophenyl)-5-methyl-pyridine-3- carbothioamide To a solution of 2-amino-6-(2-fluorophenyl)-5-methyl-pyridine-3-carbonitrile (220 mg, 0.95 mmol) in pyridine (0.22 mL) under an atmosphere of N2 was added Et ₃ N (0.12 mL, 0.95 mmol) and ammonium sulfide (0.44 mL of a 50% solution in water, 3.23 mmol). The reaction was warmed to 70 °C and stirred for 1 h. The reaction was cooled to RT and partitioned between EtOAc (30 mL) and water (15 mL). The aqueous phase was extracted with further EtOAc (30 mL). The combined organic extracts were dried over Na2SO4 and evaporated to dryness under reduced pressure to give the crude product (242mg, 95%) as a yellow solid which was used without further purification.

¹ H NMR (400 MHz, CDCh) 6 7.59 (s, 1 H), 7.44-7.33 (m, 2H), 7.32-7.22 (m, 1 H), 7.14 (ddd, 1 H), 6.09 (br s, 2H), 2.11 (d, 3H). 2H missing.

Step 5: Synthesis of 6-(2-fluorophenyl)-5-methyl-isothiazolo[3,4-b]pyridin-3- amine

To a stirred solution of 2-amino-6-(2-fluorophenyl)-5-methyl-pyridine-3- carbothioamide (0.23 g, 0.792 mmol) in MeOH (4 mL) at 0°C under an N2 atmosphere was added hydrogen peroxide solution (0.324 mL of a 30% solution in water, 3.169 mmol). The reaction was allowed to warm to RT and stirred for 18h, then re-cooled to 0°C, diluted with water and the resultant solid filtered off, washed with water and dried under vacuum to give the crude product (195mg, 93%) which was used without further purification.

¹ H NMR (400 MHz, DMSO-d6) 5 8.14 (s, 1 H), 8.09 (br s, 2H), 7.57-7.48 (m, 1 H), 7.47-7.39 (m, 1 H), 7.36-7.28 (m, 2H), 2.12 (s, 3H).

Step 6: Synthesis of Synthesis of 6-(2-fluorophenyl)-5-methyl-isothiazolo[3,4- b]pyridine (1.001)

To a stirred solution of 6-(2-fluorophenyl)-5-methyl-isothiazolo[3,4-b]pyridin-3-amin e (0.1 g, 0.378 mmol) in 1,4-dioxane (3 mL) at RT under an atmosphere of N2 was added isopentyl nitrite (0.22 mL, 1.587 mmol) dropwise over 2 minutes. The reaction mixture was then stirred at RT for 5 hours, then diluted with water and extracted with EtOAc (x 2). The combined organic extracts were dried over Na2SO4 and evaporated to dryness under reduced pressure. The crude product was purified by flash chromatography on silica gel using a gradient of EtOAc/cyclohexane as eluent followed by trituration with pentane to give the desired product (15mg, 16%).

¹ H NMR (400 MHz, CDCI3) 6 9.23 (s, 1 H), 8.01 (s, 1 H), 7.59-7.44 (m, 2H), 7.30 (t, 1 H), 7.18 (t, 1 H), 2.35 (s, 3H).

Example 2: Synthesis of 5-chloro-6-(2-fluorophenyl)isothiazolo[3,4-b]pyridine

(Compound 1.008)

Step 1 : Synthesis of 2-chloro-6-(2-fluorophenyl)pyridine-3-carbonitrile

To a solution of 2,6-dichloropyridine-3-carbonitrile (10.0 g, 57.8 mmol) in toluene (80 mL) and water (30 mL) was added K2CO3 (23.97g, 173.4 mmol) and (2- fluorophenyl)boronic acid (8.09g, 57.8 mmol). The reaction was degassed by sparging with N2 for 30 minutes and then Pd(PPh3)4 (3.34g, 2.89 mmol) added and the reaction heated at 80° under an atmosphere of N2 for 16 hours. The reaction was allowed to cool to RT and then poured into water (200 mL), filtered through a pad of celite and then extracted with EtOAc (3 x 100 mL). The combined organic extracts were dried over Na2SO4 and evaporated to dryness under reduced pressure. The crude product was purified by flash chromatography on silica gel using a gradient of EtOAc/hexane as eluent and the resultant white solid further purified by washing with TBME to give the desired product (7.50g, 56%).

Step 2: Synthesis of 2-amino-6-(2-fluorophenyl)pyridine-3-carbonitrile

To a solution of 2-chloro-6-(2-fluorophenyl)pyridine-3-carbonitrile (6.50 g, 28.0 mmol) in toluene (130 mL) was added tert-butyl carbamate (4.90g, 42.0 mmol) and caesium carbonate (14.0g, 42.0 mmol). The reaction was degassed by sparging with N2 for 15 minutes and then XPhos (4.1g, 8.4 mmol) and Pd(OAc)2 (0.94g, 4.2 mmol) were added and the reaction heated at 90°C for 16 hours under an atmosphere of N2. The reaction was allowed to cool to RT and then poured into water (200 mL), filtered through a pad of celite and then extracted with EtOAc (3 x 100 mL). The combined organic extracts were dried over Na2SO4 and evaporated to dryness under reduced pressure. The crude product was purified by flash chromatography on silica gel using a gradient of EtOAc/hexane as eluent to give the desired product (3.5g, 58%).

Step 3: Synthesis of 2-amino-5-chloro-6-(2-fluorophenyl)pyridine-3-carbonitrile

To a stirred solution of 2-amino-6-(2-fluorophenyl)pyridine-3-carbonitrile (1.56g, 7.29 mmol) in CH3CN (31 mL) was added /V-chlorosuccinimide (1.09g, 8.02 mmol) and the reaction heated at 80°C for 2 hours. The reaction was allowed to cool to RT then quenched by addition of saturated aqueous NaHCOs (50 mL) and extracted with EtOAc (3 x 100 mL). The combined organic extracts were dried over Na2SO4 and evaporated to dryness. The crude product was purified by flash chromatography on silica gel using a gradient of EtOAc/hexane as eluent to give the desired product (1.0g, 49.8%).

Step 4: Synthesis of 2-amino-5-chloro-6-(2-fluorophenyl)pyridine-3- carbothioamide

To a stirred solution of 2-amino-5-chloro-6-(2-fluorophenyl)pyridine-3-carbonitrile (500mg, 2.02 mmol) in pyridine (0.5 mL) at RT under an N2 atmosphere was added Et ₃ N (0.27 mL, 2.02 mmol) and ammonium sulfide (1.0 mL of a 48% w/w solution in water, 7.04 mmol). The reaction was heated to 70°C for 1 hour, allowed to cool to RT then diluted with water (15 mL) and extracted with EtOAc (2 x 30 mL). The combined organic extracts were dried over Na2SO4 and evaporated to dryness to give the crude product which was used in the next step without further purification.

Step 5: Synthesis of 5-chloro-6-(2-fluorophenyl)isothiazolo[3,4-b]pyridin-3- amine

To a solution of 2-amino-5-chloro-6-(2-fluorophenyl)pyridine-3-carbothioamide (600mg, 2.13 mmol) in MeOH (9.6 mL) at 0°C was added H2O2 (0.87 mL of a 30% w/w solution in water, 8.52 mmol). The reaction was allowed to warm to RT and stirred for 18 hours. The reaction was cooled to 0°C then diluted with water and the resultant solid removed by filtration, washed with water and air dried. The crude product was purified by flash chromatography on silica gel using a gradient of EtOAc/hexane as eluent to give the desired product (250mg, 41.1%). Step 6: Synthesis of 5-chloro-6-(2-fluorophenyl)isothiazolo[3,4-b]pyridine

(1.008)

To a solution of 5-chloro-6-(2-fluorophenyl)isothiazolo[3,4-b]pyridin-3-amine (150mg, 0.54 mmol) at RT in DMF (1.5 mL) under an atmosphere of N2 was added dropwise a solution of tert-butyl nitrite (0.13 mL, 1.07 mmol) in DMF (0.75 mL). The reaction was stirred at RT for 1 hour, then diluted with water (20 mL) and extracted with EtOAc (3 x 30 mL). The combined organic extracts were dried over Na2SO4 and evaporated to dryness. The crude product was purified by flash chromatography on silica gel using a gradient of EtOAc/hexane as eluent to give the desired product (43mg, 27.3%).

¹ H NMR (400 MHz, CDCh) 6 9.33 (s, 1 H), 8.29 (s, 1 H), 7.62-7.55 (m, 1 H), 7.54-7.46

(m, 1 H), 7.31 (t, 1 H), 7.20 (t, 1H)

Table 1. Compounds of the present invention

Biological Examples

Seeds of a variety of test species are sown in standard soil in pots Amaranthus palmeri (AMAPA), Amaranthus retoflexus (AMARE), Setaria faberi (SETFA), Echinochloa crus-galli (ECHCG), Ipomoea hederacea (IPOHE)). After cultivation for one day (pre-emergence) or after 8 days cultivation (post-emergence) under controlled conditions in a glasshouse (at 24/16°C, day/night; 14 hours light; 65% humidity), the plants are sprayed with an aqueous spray solution derived from the formulation of the technical active ingredient in acetone I water (50:50) solution containing 0.5% Tween 20 (polyoxyethelyene sorbitan monolaurate, CAS RN 9005- 64-5). Compounds are applied at 1000 g/ha unless otherwise stated. The test plants are then grown in a glasshouse under controlled conditions in a glasshouse (at 24/16°C, day/night; 14 hours light; 65% humidity) and watered twice daily. After 13 days for pre and post-emergence, the test is evaluated for the percentage damage caused to the plant. The biological activities are shown in the following table on a five-point scale (5 = 81-100%; 4 = 61-80%; 3=41-60%; 2=21-40%; 1=0-20%).

TABLE B1. Post-emergence Test

TABLE B2. Pre-emergence Test

NT = Not Tested. COMPARATIVE TEST

Seeds of test species were sown in standard soil in pots. After cultivation for one day under controlled conditions in a glasshouse (at 24/16°C, day/night; 14 hours light; 65 % humidity), the plants were sprayed with an aqueous spray solution derived from the formulation of the technical active ingredient in 0.6 ml acetone and 45 ml formulation solution containing 10.6% Emulsogen EL (Registry number 61791-12-6), 42.2% N-methyl pyrrolidone, 42.2% dipropylene glycol monomethyl ether (CAS RN 34590-94-8) and 0.2 % X-77 (CAS RN 11097-66-8).

The test plants were then grown in a glasshouse under controlled conditions in a glasshouse (at 24/16°C, day/night; 14 hours light; 65 % humidity) and watered twice daily. After 14 days for post-emergence and 21 days for pre-emergence, the test was evaluated (100 = total damage to plant; 0 = no damage to plant).

Test species: Amaranthus retoflexus (AMARE); Glycine max (GLXMA); Zea Mays (ZEAMX).

TABLE B3. Pre-emergence Test TABLE B4. Post-emergence Test

C1 is compound I-002 disclosed in WO2021/204589. As can be seen, the compounds of the invention show improved crop selectivity compared to the compound C1 known from WO2021/204589 whilst retaining comparable levels of weed control.